Summary/High Level Thoughts

To start, I'll admit that when I read this, I wasn't in a real position to leverage everything that was being talked about, which is likely why I didn't give it higher than an 8.

That said, this is the kind of book you refer back to throughout your life in business, and I think it has the most relevance for a) an entrepreneur who is scaling up, and building a large organization, or b) someone already working in a large organization, managing a relatively large department and therefore number of people.

Very actionable advice in many areas, and certainly well thought out and methodical. Definitely recommend, just keep in mind the ideal reader profiles above.

Favourite Quotes

"This is not checkers, this is motherfuckin’ chess"

"Don’t take it personally"

Detailed Notes

Most business relationships either become too tense to tolerate or not tense enough to be productive after a while

Most important rule of raising money privately: look for market of one

You need 2 types of friends: person who will be over the moon excited when good things happen, and those you can rely on when life is on the line and you have one call

“If you’re going to eat shit, don’t nibble”

Ask yourself “what am I not doing [/providing]?”

When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it.

‘The Struggle’ passage

“Life is struggle” - Karl Marx

p. 56 - Some Stuff That May or May Not Help

Don’t put it all on your shoulders

This is not checkers, this is motherfuckin’ chess

Play long enough and you might get lucky

Don’t take it personally

Remember that this is what separates the women from the girls

Tell it like it is, because:

Trust: without trust, communication breaks

The more brains working on hard problems, the better

A good culture is like the old RIP routing protocol; bad news travels fast; good news travels slow.

If you run a company, you will experience overwhelming psychological pressure to be overly positive. Stand up to the pressure, face your fear, and tell it like it is.

How to lay off employees the right way:

Get your head right

Don’t delay

Be clear in your own mind about why you are laying people off

Train your managers: they need to lay off their own people

Explain what happened and company, not personal failure

They should be clear: employee impacted and non-negotiable

Fully prepped with details about benefits and support

Address the entire company (before layoffs and message is for those who are staying)

Be visible, be present

Firing an executive:

Root cause analysis

Inform the board

Prepare for conversation

Preparing company communication

Once you make the decision, consider 2 deep emotions:

Embarrassment and betrayal

Keys to being fair and honest in this situation (p. 68):

Use appropriate language

Admit reality

Acknowledge the contributions

“There may be nothing scarier in business than facing an existential threat. So scary that many in the organization will do everything to avoid facing it. They will look for any alternative, any way out, any excuse not to live or die in a single battle.”

“If our company isn’t good enough to win, then do we need to exist at all?”

“I don’t give a fuck how well-trained you are. If you don’t bring me $500K a quarter, I’m putting a bullet in your head.”

“We take care of the people, the products, and the profits - in that order.”

Why you should train your people:

Productivity

Performance management

Product quality

Retention of employee

Implementing training

Needs to be mandatory

“If you would be shocked and horrified if company X hired several of your employees, then you should not hire any of theirs”

p. 91 - what to look for when screening executive candidates

Managing strictly by numbers is like painting by numbers - strictly for amateurs

Common management debt sources:

Putting two in the box

Overcompensating key employee because she gets another job offer

No performance management or employee feedback process

“Every really good, really experienced CEO I know shares 1 important characteristic: they tend to opt for the hard answer to organizational issues”

P. 101 - list of questions great HR organization can answer

Keeping politics out:

Hire people with right kind of ambition (for company success)

Build strict processes for potentially political issues and do not deviate

Peter principle: in a hierarchy, members are promoted so long as they work competently; sooner or later they will become incompetent

Law of Crappy People: for any title level in a large organization, the talent on that level will eventually converge to the crappiest person with that title

Questions for one-on-ones: p. 123

Go for shock when designing culture

Perks are not culture; they don’t establish a core value that drives the business and helps promote it in perpetuity

Steps to the organizational design: p.129

Check out first chapter of “High Output Management” for process design

“Managing at scale is a learned skill rather than a natural ability”

WFIO (whiff-ee-yo): we’re fucked, it’s over

Calming nerves: make friends, get it on paper, focus on the road (not the wall)

Someone needs to be in charge (one person)

Courage, like character, can be developed

Decision tables: p. 144

2 skills to run organization: knowing what to do, getting company do to what you know

Measure of quality of leader: quantity, quality and diversity of people who want to follow her